Water → 2-tert-butyl-4-fluoro-1H-indol-5-amine

HRID 1908426Notes

Reaction equation

HRID 1908426 reaction equation
[C:1]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[C:11]([F:14])[C:10]([N+:15]([O-])=O)=[CH:9][CH:8]=2)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].O>CO.Cl[Ni]Cl>[C:1]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[C:11]([F:14])[C:10]([NH2:15])=[CH:9][CH:8]=2)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 534211832-Tert-butyl-4-fluoro-5-nitro-1H-indole

Product 1

HCID 591292452-tert-butyl-4-fluoro-1H-indol-5-amineYield 50%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-tert-butyl-4-fluoro-5-nitro-1H-indole (2.1 g, 9.0 mmol) in methanol (50 mL) was added NiCl2 (4.2 g, 18 mmol) and NaBH4 (1.0 g, 27 mmol) at 0° C. After the addition, the mixture was stirred for 5 min. Water (20 mL) was added and the mixture was extracted with EtOAc (30 mL×3). The organic layers were washed with sat. NaCl and water, dried over anhydrous Na2SO4, evaporated under vacuum to give 2-tert-butyl-4-fluoro-1H-indol-5-amine (900 mg, 50%). 1H NMR (300 MHz, CDCl3) δ 7.80 (brs, 1H), 6.91 (d, J=8.4 Hz, 1H), 6.64 (dd, J=0.9, 2.4 Hz, 1H), 6.23 (s, 1H), 1.38 (s, 9H).

Workup

  1. additionAfter the addition
  2. extractionthe mixture was extracted with EtOAc (30 mL×3)
  3. washThe organic layers were washed with sat. NaCl and water
  4. dry with materialdried over anhydrous Na2SO4
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-25b52de22ecb4b2eac8e81d267d099f7
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

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